Polyglycol ethers of z



Patented Mar. 2, 1954 POLYGLYCOL ETHERS OF 2,6,8-TRIMETHYL- lglglgNOLA AND PROCESS OF MAKING Milton Kosmin, Dayton, Ohio, assignor to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware 1 1 v No Drawing. Application October 20, 1950, Serial No. 191,319

5 Claims. (Cl. 260-615) The present invention relates to compounds having high surface-activity in aqueous solutions and to processes for preparing the said products as determined by the Harris method is illustrated in the following table:

compounds. 1

In my prior Patents Nos. 2,508,035 and s DetergencyyPemntofeardmol 2,508,036,-issued May 16; 1950, I have disclosed polyglycol ethers of certain branched chain al- Pmdmt'rested 100% Acme cohols, namely, 5-ethylnonanol-2 and Z-n-propyl- I heptanol. These products are produced by con- $9 ,393, 39 2% densingethylene oxide with the respective al- 10 cohols. While these compounds show especially zn.1 mpy1.heptano1+5 moles low and therefore advantageous wetting out 1;v1en oxi en 50 45 111 10s speeds when aqueous solutions thereof are tested fig yfi gisfijii ffffi 100 1. 99 109 by the Braves test, these products have been P 87 93 109 found; to be somewhat deficient in detergency. l5 fi g g gfi fii ggigigg555 2 I ,Ilhave 110W found that if at least 5, but less ;ig 36 37 106 112 thgfln'zlqmoles of {ethylene Oxide can be 6011- -%ls ;lei ie-oxlde-;l -114 110 110 111 densed with. 2,6,8- trunethylnonanol-4 thata segf fff no 101 116 ries of. products is obtained WhlCh exhibit not 2,6,8-Trimethylnpnan +5 I only excellent wetting out properties but also ex- 3 33%?ffgi fiflgffifig gfij g mg 94 107 m cellent detergency. As a matter of fact, the de- 2 g g ayt 111 101 108 108 tersency oflthfi, present Pr s sup ri r t $1012; tfi i e fi gff i n 10 102 102 108 5 that of the cprresponq-mg products made from 2 i ies e tii y leng 100' 101 102 a 103 theabove alcohols. I

" Relative detergency may be measured by a y 'Ihe builder consisted 0140 parts of tetrasodium pyrophosphate, quantitative method; however for the purpos of parts of starch for each 20 parts of the active constituent. evaluating the present and related products I have used the method described by Jay C. Harris g gs g izii ggz xzfi f i figg gi' ggggz z gig g i g g :g 30 until at least 5 moles, but not in excess of 20 ep em y e app of 18 moles, have been condensed with the alcohol. method it is possible to evaluate the detergency The condensation may be carried out by mixing of a Producfi in terms of any Standard detergent ethylene oxide either as gas or liquid with the For convemence Ihave compared the detrgency alcohol and heating to a temperature of from of the prese t nd related products Wlth t to 170 0. The condensation reaction is aided detergency of Gardmol, which is a commercial by the presence of a catalyst. For this purpose t ent pro ct produced by Sulf ing the alany alkaline material, such as an alkali metal cohols derived by hydrogenation of cocoanut oil hydroxide or alcoholate may be used. The catafatty acids. lyst may be employed in relatively small amounts, The detergency of the present and related 40 usually from 0.5% to 1% being employed. The

4 1 catalyst is added to the liquid alcohol at the beginning of the reaction.

The products so produced are secondary alcohol ethers and are believed to have the strucin which n is an integer having a value of from 4 to 19.

The following examples will further illustrate this invention:

' EXAMPLE 1 1042 g. (5.6 moles) of 2,6,8-trimethylnonanol-4 was placed in a glass flask, 10.4 g. of powdered KOH added and the contents then heated to 130 C. ltstneam of gaseous ethylene oxide was pa s in o the a o o eans of 1 isas ed persing tube and the stream continued until 1865 g. of ethylene oxide had combined. The mass became hot due to the exothermic reaction and the temperature wascoritrolled-by codling the flask by the application =ofco1dwa=ter-to the exterior. In this way the temperature was maintained at about 150 C ..--.during@theprogress;

of the reaction. a

The product obtained corresponds to the pentaethylene glycol ether of 2,6,8-trimethylnonangl-$. V

EXAMPLE 2 A portion of the product obtained above,

wei h n i959 .gwa i i ther treated ith 2.86 .2:- df Ethylene Oxide i. si th sa a paratuses described above. There was thus obtained a $5 :-1 molar ratio ethylene oxide-2.6,8-trimethyl nonanolel condensation product.

- {EXAMPLE 3 ,..l portion of-.the product obtained in Example 2,- .weighing: 915g.- .wasqfurther treated with 194 g.

of-ethylene .-oxide -using -t-he same apparatus-as described above. The product @obtained i'COlfPB- spondedto the decaethylene.glycoLetherpf 1.2.533.- trimethylnonanol-ge.

I EXAMPLE .4 w 1 A portion, ofthe p duct o tain d in samfil 3 weighing 4.511 g. was treated with 'leo g fethy r ene oxide in the manner .descri-bedzabove.

*productcorresponded to thepenta'decylethylene glycol ether. of, 2,6,8etrimethylnonanol zl.

.The speed .of wetting, as -measured Z2123 11,19 'Draves test of the products who. dissolve following "water-ft) form a 0.5% solution gave =-t-he values:

umber imam-e fillets l.'6 fi31 LYQun MWRWnNMFlilac-112d, 1 29- .l'.97Q;5,-78 finha ler .et .al. eiig- 1934 2164331 ficjhoeller .eLt al-a a, .uly 24,119.39 29 26119 fzDe'i Gltoote et a1. Tiles-12a, I931!) 2:316:84; Co1eman1, 'Aug.- 2Q; 1953 2355;823 scl'ilegel Aug.3'15 ;"1344 enemas uKosmi-n {May "1- 21 950 2,527,970 Sokol Qe't; .31; @1950 Table S cod 0! Product Tested Petting, Seconds Example 1 4. 0 Example 2- 3. 7 Example 3 3. 4 Example 4 4. 4

What I claim is: 1. Compounds having the formula:

in which n has a value of at least 4 but not in excess of 20.

2. .qo noundah ne tb -iormu a:

0 v v (JJ'zHlOhOzHlOH "3. Compoundshaving the formula:

.0 Ha .3 CH1 .ciufiincgfcnomcnomcnom amrn'ronunosmm. 

1. COMPOUND HAVING FORMULA: 